2,2-Dimethoxypropane → HCID 21849167, compound

HRID 617891Notes

Reaction equation

HRID 617891 reaction equation
[C:1]([NH:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][CH:11]=1)([CH2:8][OH:9])[CH2:6][OH:7])(=[O:3])[CH3:2].CO[C:28](OC)([CH3:30])[CH3:29].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[C:1]([NH:4][C:5]1([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][CH:11]=2)[CH2:8][O:9][C:28]([CH3:30])([CH3:29])[O:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 69252-Methylbenzenesulfonic acidHCID 21849172HCID 21849172, compound

Product 1

HCID 21849167HCID 21849167, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Acetylamino-2-(4-decylphenyl)-1,3-propanediol (224 mg) and 2,2-dimethoxypropane (0.3 ml) were dissolved in benzene (5 ml) and the mixture was refluxed under heating in the presence of a catalytic amount of toluenesulfonic acid. After cooling, the reaction mixture was washed with an aqueous sodium hydrogencarbonate solution and dried over sodium sulfate. The solvent was distilled away and the residue was purified by preparative thin layer chromatography (silica gel) to give 99 mg of the amorphous subject compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with an aqueous sodium hydrogencarbonate solution
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue was purified by preparative thin layer chromatography (silica gel)

Sources & evidence

ORD record
ord-31da5979c16f43e9a4301ca55853e89f
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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